CA2658911A1 - Pyrimidine compounds for combating pathogenic fungi and cancer - Google Patents

Info

Publication number

CA2658911A1

CA2658911A1 CA002658911A CA2658911A CA2658911A1 CA 2658911 A1 CA2658911 A1 CA 2658911A1 CA 002658911 A CA002658911 A CA 002658911A CA 2658911 A CA2658911 A CA 2658911A CA 2658911 A1 CA2658911 A1 CA 2658911A1

Authority

CA

Canada

Prior art keywords

alkyl

group

formula

alkoxy

radical

Prior art date

2006-08-02

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 150000003230 pyrimidines Chemical class 0.000 title claims abstract description 30
• 206010028980 Neoplasm Diseases 0.000 title claims description 6
• 201000011510 cancer Diseases 0.000 title claims description 6
• 244000053095 fungal pathogen Species 0.000 title abstract description 3
• -1 heteroaromatic radical Chemical class 0.000 claims description 720
• 150000001875 compounds Chemical class 0.000 claims description 609
• 229910052736 halogen Inorganic materials 0.000 claims description 187
• 150000003254 radicals Chemical group 0.000 claims description 172
• 150000002367 halogens Chemical group 0.000 claims description 145
• 229910052757 nitrogen Inorganic materials 0.000 claims description 124
• 125000001424 substituent group Chemical group 0.000 claims description 112
• 125000005842 heteroatom Chemical group 0.000 claims description 92
• 229910052717 sulfur Inorganic materials 0.000 claims description 87
• 125000000623 heterocyclic group Chemical group 0.000 claims description 82
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 80
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 75
• 229910052739 hydrogen Inorganic materials 0.000 claims description 74
• 229920006395 saturated elastomer Polymers 0.000 claims description 74
• 125000003118 aryl group Chemical group 0.000 claims description 62
• 229910052799 carbon Inorganic materials 0.000 claims description 61
• 229910052760 oxygen Inorganic materials 0.000 claims description 61
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 60
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 51
• 239000001257 hydrogen Substances 0.000 claims description 50
• 239000000203 mixture Substances 0.000 claims description 47
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 35
• 150000003839 salts Chemical class 0.000 claims description 30
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 29
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 26
• 125000004432 carbon atom Chemical group C* 0.000 claims description 25
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 24
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 24
• 125000001624 naphthyl group Chemical group 0.000 claims description 24
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 23
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 21
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 21
• 125000001931 aliphatic group Chemical group 0.000 claims description 20
• 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 19
• 239000001301 oxygen Substances 0.000 claims description 18
• 241000233866 Fungi Species 0.000 claims description 17
• 125000002723 alicyclic group Chemical group 0.000 claims description 16
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 16
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
• 125000004429 atom Chemical group 0.000 claims description 15
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 14
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 14
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 13
• 125000001072 heteroaryl group Chemical group 0.000 claims description 13
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 12
• 230000000855 fungicidal effect Effects 0.000 claims description 12
• 125000004076 pyridyl group Chemical group 0.000 claims description 12
• 239000011593 sulfur Chemical group 0.000 claims description 12
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 11
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 11
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 11
• 125000004682 aminothiocarbonyl group Chemical group NC(=S)* 0.000 claims description 11
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
• 150000001721 carbon Chemical group 0.000 claims description 10
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 9
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 9
• 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims description 8
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 8
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 8
• 125000004104 aryloxy group Chemical group 0.000 claims description 7
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 7
• 125000001425 triazolyl group Chemical group 0.000 claims description 7
• 239000007787 solid Substances 0.000 claims description 6
• 125000000335 thiazolyl group Chemical group 0.000 claims description 6
• 125000001544 thienyl group Chemical group 0.000 claims description 6
• 125000005110 aryl thio group Chemical group 0.000 claims description 5
• 125000002883 imidazolyl group Chemical group 0.000 claims description 5
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 5
• 239000007788 liquid Substances 0.000 claims description 5
• 125000002971 oxazolyl group Chemical group 0.000 claims description 5
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 4
• 125000001651 cyanato group Chemical group [*]OC#N 0.000 claims description 4
• 125000002541 furyl group Chemical group 0.000 claims description 4
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 4
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 4
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
• 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 4
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 4
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 4
• 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 4
• 125000004306 triazinyl group Chemical group 0.000 claims description 4
• 150000001602 bicycloalkyls Chemical group 0.000 claims description 3
• 125000004122 cyclic group Chemical group 0.000 claims description 3
• 239000003814 drug Substances 0.000 claims description 3
• 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 3
• 239000008194 pharmaceutical composition Substances 0.000 claims description 3
• 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 2
• 150000005840 aryl radicals Chemical class 0.000 claims description 2
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
• 239000003937 drug carrier Substances 0.000 claims description 2
• 125000004043 oxo group Chemical group O=* 0.000 claims description 2
• 125000003003 spiro group Chemical group 0.000 claims description 2
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 15
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 14
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 10
• 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 8
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 8
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 7
• 125000005865 C2-C10alkynyl group Chemical group 0.000 claims 7
• 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 6
• 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims 5
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 5
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 5
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 5
• 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 4
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 4
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 4
• 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims 3
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 3
• 125000004750 (C1-C6) alkylaminosulfonyl group Chemical group 0.000 claims 2
• 241000352333 Amegilla alpha Species 0.000 claims 2
• 241001334141 Rugopharynx alpha Species 0.000 claims 2
• 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims 1
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
• UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 claims 1
• UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 claims 1
• 241001367053 Autographa gamma Species 0.000 claims 1
• 241000518994 Conta Species 0.000 claims 1
• 241001098636 Trichogramma alpha Species 0.000 claims 1
• 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
• 239000000417 fungicide Substances 0.000 abstract description 12
• 239000008177 pharmaceutical agent Substances 0.000 abstract 1
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 427
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 120
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 102
• 239000000460 chlorine Substances 0.000 description 77
• 229910052801 chlorine Inorganic materials 0.000 description 73
• 125000005843 halogen group Chemical group 0.000 description 50
• 238000006243 chemical reaction Methods 0.000 description 43
• 125000001309 chloro group Chemical group Cl* 0.000 description 42
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 40
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 37
• 239000011737 fluorine Substances 0.000 description 35
• 229910052731 fluorine Inorganic materials 0.000 description 35
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 35
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 35
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 34
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 32
• 125000000217 alkyl group Chemical group 0.000 description 31
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 30
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 29
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 28
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
• 150000002431 hydrogen Chemical class 0.000 description 25
• 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 23
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
• 229910003827 NRaRb Inorganic materials 0.000 description 20
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 19
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 19
• 229910052794 bromium Inorganic materials 0.000 description 19
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
• 241000196324 Embryophyta Species 0.000 description 18
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
• CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 18
• 238000000034 method Methods 0.000 description 18
• OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 17
• 235000013339 cereals Nutrition 0.000 description 17
• 239000002904 solvent Substances 0.000 description 17
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 16
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 16
• 239000002253 acid Substances 0.000 description 16
• 239000002585 base Substances 0.000 description 16
• 239000003921 oil Substances 0.000 description 16
• 235000019198 oils Nutrition 0.000 description 16
• 238000002360 preparation method Methods 0.000 description 16
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
• 240000007594 Oryza sativa Species 0.000 description 15
• 235000007164 Oryza sativa Nutrition 0.000 description 15
• 238000009472 formulation Methods 0.000 description 15
• 235000009566 rice Nutrition 0.000 description 15
• 239000000243 solution Substances 0.000 description 15
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
• 240000008042 Zea mays Species 0.000 description 14
• 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 14
• 235000002017 Zea mays subsp mays Nutrition 0.000 description 14
• 235000005822 corn Nutrition 0.000 description 14
• 229910052783 alkali metal Inorganic materials 0.000 description 13
• 125000003545 alkoxy group Chemical group 0.000 description 13
• 239000000047 product Substances 0.000 description 13
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 13
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
• 239000006185 dispersion Substances 0.000 description 12
• 239000000839 emulsion Substances 0.000 description 11
• 230000008569 process Effects 0.000 description 11
• 239000000725 suspension Substances 0.000 description 11
• 210000004027 cell Anatomy 0.000 description 10
• 238000010790 dilution Methods 0.000 description 10
• 239000012895 dilution Substances 0.000 description 10
• 239000000463 material Substances 0.000 description 10
• 239000000843 powder Substances 0.000 description 10
• 125000006238 prop-1-en-1-yl group Chemical group [H]\C(*)=C(/[H])C([H])([H])[H] 0.000 description 10
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
• 125000004453 alkoxycarbonyl group Chemical group 0.000 description 9
• 239000000969 carrier Substances 0.000 description 9
• 125000000753 cycloalkyl group Chemical group 0.000 description 9
• 125000001188 haloalkyl group Chemical group 0.000 description 9
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 9
• 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 9
• 241000894007 species Species 0.000 description 9
• 235000013311 vegetables Nutrition 0.000 description 9
• 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 8
• 239000004215 Carbon black (E152) Substances 0.000 description 8
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 8
• 125000003342 alkenyl group Chemical group 0.000 description 8
• 125000000304 alkynyl group Chemical group 0.000 description 8
• 125000000392 cycloalkenyl group Chemical group 0.000 description 8
• 239000002270 dispersing agent Substances 0.000 description 8
• 239000008187 granular material Substances 0.000 description 8
• 229930195733 hydrocarbon Natural products 0.000 description 8
• 229910052740 iodine Inorganic materials 0.000 description 8
• 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 7
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 7
• 150000007513 acids Chemical class 0.000 description 7
• 239000003795 chemical substances by application Substances 0.000 description 7
• 125000000000 cycloalkoxy group Chemical group 0.000 description 7
• 229910052702 rhenium Inorganic materials 0.000 description 7
• 238000012360 testing method Methods 0.000 description 7
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
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• 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 6
• 125000004917 3-methyl-2-butyl group Chemical group CC(C(C)*)C 0.000 description 6
• BMTZEAOGFDXDAD-UHFFFAOYSA-M 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholin-4-ium;chloride Chemical compound [Cl-].COC1=NC(OC)=NC([N+]2(C)CCOCC2)=N1 BMTZEAOGFDXDAD-UHFFFAOYSA-M 0.000 description 6
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
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• 235000010469 Glycine max Nutrition 0.000 description 6
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
• 125000003302 alkenyloxy group Chemical group 0.000 description 6
• 230000015572 biosynthetic process Effects 0.000 description 6
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• 230000000694 effects Effects 0.000 description 6
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• 125000001153 fluoro group Chemical group F* 0.000 description 6
• 125000000262 haloalkenyl group Chemical group 0.000 description 6
• 125000005291 haloalkenyloxy group Chemical group 0.000 description 6
• 125000004438 haloalkoxy group Chemical group 0.000 description 6
• 125000000232 haloalkynyl group Chemical group 0.000 description 6
• 125000005292 haloalkynyloxy group Chemical group 0.000 description 6
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• 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 6
• 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 description 6
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 6
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• 238000003786 synthesis reaction Methods 0.000 description 6
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• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 5
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• CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 description 5
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• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
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• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 5
• 229910052701 rubidium Inorganic materials 0.000 description 5
• 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
• 125000006765 (C2-C6) haloalkenyloxy group Chemical group 0.000 description 4
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• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
• PZBPKYOVPCNPJY-UHFFFAOYSA-N 1-[2-(allyloxy)-2-(2,4-dichlorophenyl)ethyl]imidazole Chemical compound ClC1=CC(Cl)=CC=C1C(OCC=C)CN1C=NC=C1 PZBPKYOVPCNPJY-UHFFFAOYSA-N 0.000 description 4
• HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 4
• WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 4
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 4
• 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 4
• 125000005916 2-methylpentyl group Chemical group 0.000 description 4
• 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 4
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